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Occurrence of a New Generation of Disinfection Byproducts Environ. Sci. Technol. 2006, 40, 7175-7185 Occurrence of a New Generation of the formation of trihalonitromethanes. In addition to the ² chlorinated furanones that have been measured previously, Disinfection Byproducts brominated furanonesswhich have seldom been analyzeds were detected, especially in high-bromide waters. The STUART W. KRASNER,*,³ presence of bromide resulted in a shift to the formation HOWARD S. WEINBERG,§ of other bromine-containing DBPs not normally measured SUSAN D. RICHARDSON,| SALVADOR J. (e.g., brominated ketones, acetaldehydes, nitromethanes, PASTOR,³ RUSSELL CHINN,³ acetamides). Collectively, ∼30 and 39% of the TOX and total MICHAEL J. SCLIMENTI,³ organic bromine, respectively, were accounted for (on a § GRETCHEN D. ONSTAD, AND median basis) by the sum of the measured halogenated DBPs. ALFRED D. THRUSTON, JR.| In addition, 28 new, previously unidentified DBPs were Metropolitan Water District of Southern California, detected. These included brominated and iodinated haloacids, 700 Moreno Avenue, La Verne, California 91750-3399, Department of Environmental Sciences and a brominated ketone, and chlorinated and iodinated Engineering, University of North Carolina, aldehydes. Chapel Hill, North Carolina 27599-7431, and National Exposure Research Laboratory, U.S. Environmental Protection Agency, 960 College Station Road, Athens, Georgia 30605 Introduction Approximately 600-700 disinfection byproducts (DBPs) have been reported in the literature for the major disinfectants used (chlorine, ozone, chlorine dioxide, chloramines) as well A survey of disinfection byproduct (DBP) occurrence in as their combinations (1-3). Of these DBPs, only a small the United States was conducted at 12 drinking water percentage has been quantified in drinking waters. DBP treatment plants. In addition to currently regulated DBPs, surveys in the United States in the 1980s and 1990s provided more than 50 DBPs that rated a high priority for potential data for assessing a new maximum contaminant level (MCL) toxicity were studied. These priority DBPs included iodinated for trihalomethanes (THMs) as well as to develop regulations for other DBPs. In 1985, the U.S. Environmental Protection trihalomethanes (THMs), other halomethanes, a nonregulated Agency (EPA) measured chlorination DBPs at 10 operating haloacid, haloacetonitriles, haloketones, halonitromethanes, utilities, utilizing both target compound and broad-screen haloaldehydes, halogenated furanones, haloamides, analyses (2). The halogenated compounds, cumulatively, and nonhalogenated carbonyls. The purpose of this study accounted for between 30 and 60% of the total organic was to obtain quantitative occurrence information for halogen (TOX) found in these samples. In 1988-1989, a study new DBPs (beyond those currently regulated and/or studied) of 35 U.S. utilities was conducted, which analyzed for 19 for prioritizing future health effects studies. An effort halogenated DBPs and two aldehydes (3). On a weight basis, was made to select plants treating water that was high in THMs were the largest class of DBPs detected; the second total organic carbon and/or bromide to enable the largest fraction was haloacetic acids (HAAs). In addition, Glaze detection of priority DBPs that contained bromine and/or and Weinberg studied the formation of ozonation DBPs at 10 North American utilities in 1990-1991 (4). This study iodine. THMs and haloacetic acids (HAAs) represented the demonstrated that aldehydes could be removed with bio- two major classes of halogenated DBPs formed on a filtration (5), and bromate formation could be minimized at weight basis. Haloacetaldehydes represented the third a lower ozonation pH (6). major class formed in many of the waters. In addition to In 1997-1998, 296 U.S. utilities operating a total of 500 obtaining quantitative occurrence data, important new plants conducted a DBP survey under the Information information was discovered or confirmed at full-scale plants Collection Rule (ICR) (7). This survey included measurements on the formation and control of DBPs with alternative for the 4 regulated THMs, 6-9 HAAs (5 are regulated), 4 disinfectants to chlorine. Although the use of alternative haloacetonitriles, 2 haloketones, trichloronitromethane (chlo- Downloaded via UNIV OF SOUTHERN CALIFORNIA on October 15, 2018 at 17:55:34 (UTC). disinfectants (ozone, chlorine dioxide, and chloramines) ropicrin), trichloroacetaldehyde (chloral hydrate), cyanogen See https://pubs.acs.org/sharingguidelines for options on how to legitimately share published articles. minimized the formation of the four regulated THMs, chloride, chlorite, chlorate, bromate, glyoxal, methyl glyoxal, trihalogenated HAAs, and total organic halogen (TOX), and 11 other aldehydes. The ICR, which included the same DBPs from the earlier studies (3, 4), greatly expanded our several priority DBPs were formed at higher levels with knowledge on the occurrence of these DBPs. the alternative disinfectants as compared with chlorine. For Other DBPs of health concern have had less extensive s example, the highest levels of iodinated THMs which monitoring. The chlorinated furanone 3-chloro-4-(dichlo- are not part of the four regulated THMsswere found at a romethyl)-5-hydroxy-2-(5H)-furanone (MX) has been mea- plant that used chloramination with no prechlorination. sured in a limited number of studies in the United States (8, The highest concentration of dichloroacetaldehyde was at 9) and elsewhere (10). For example, Kronberg and colleagues a plant that used chloramines and ozone; however, this found from 15 to 67 ng/L of MX in chlorinated drinking water disinfection scheme reduced the formation of trichloro- from three towns in Finland (10). MX, its geometric isomer acetaldehyde. Preozonation was found to increase (E)-2-chloro-3-(dichloromethyl)-4-oxobutenoic acid (EMX), and their oxidized and reduced forms were found in U.S. ² This article is part of the Emerging Contaminants Special Issue. waters (11), while MX and brominated analogues of MX * Corresponding author phone: (909)392-5083; fax: (909)392-5246; (BMXs) have been identified in Japanese drinking waters e-mail: [email protected]. ³ Metropolitan Water District of Southern California. (12). § University of North Carolina. Trihalonitromethanes with bromine have been identified | U.S. Environmental Protection Agency. in bench-scale chlorination studies (13), and bromopicrin 10.1021/es060353j CCC: $33.50 2006 American Chemical Society VOL. 40, NO. 23, 2006 / ENVIRONMENTAL SCIENCE & TECHNOLOGY 9 7175 Published on Web 07/26/2006 was detected in pilot-plant studies after ozone treatment Experimental Methods (14). In addition to trihalonitromethanes, mono- and diha- Chemical Standards. A number of the priority DBPs were logenated nitromethanes were identified in pilot-scale studies synthesized for this study (Supporting Information) (22, 26). of chlorine and chloramines, with and without preozonation Since the project began, some of the standards have become (15, 16). Brominated trihaloacetaldehydes have been found commercially available (Orchid Helix, New Westminster, BC, in chlorinated fulvic acid solutions containing bromide (17), Canada). Other synthesized standards used to confirm and iodinated THMs have been reported in chlorinated and broadscreen identifications were provided by CanSyn Chem chloraminated drinking water (18-21). Iodinated THM Corp. (Toronto, ON, Canada). All other chemicals and formation in bench- and plant-scale studies was favored by reagents were purchased at the highest level of purity from chloramination, especially if the ammonia was added first. Acros Organics (Pittsburgh, PA), Aldrich Chemical Co. Because many of the non-ICR DBPs have only been (Milwaukee, WI), ChemService (West Chester, PA), Fluka studied at bench scale or in limited full-scale surveys, there Chemical Co. (Ronkonkoma, NY), Mallinckrodt (Phillipsburg, is significant uncertainty over the identity and levels of NJ), Sigma Chemical Company (St. Louis, MO), Supelco DBPs that people are exposed to in their drinking water. (Bellefonte, PA), TCI America (Portland, OR), or Ultra Moreover, only a limited number of DBPs have been studied Scientific (North Kingston, RI) (23, 26). for adverse health effects because such studies are extremely expensive. Analytical Methods. A brief description of the analytical methods follows; more extensive details can be found in the To focus this research, an expert toxicology review of the Supporting Information. Most of the halogenated DBPss ∼500 DBPs reported in the literature (as of 1998) was THMs, tribromochloromethane, haloacetonitriles, haloke- conducted (22) with an in-depth mechanism-based structural tones, di- and trihalogenated acetaldehydes, halonitrometh- activity relationship analysisssupplemented by an extensive anes, tetrabromochloroethane, and benzyl chlorideswere literature search for genotoxicity and other datasused to analyzed for and quantified using a liquid/liquid extraction rank the carcinogenic potential of these DBPs. Approximately (LLE)-gas chromatography (GC)/electron capture detection 50 DBPs that received the highest ranking for potential (ECD) method (23, 26). A purge-and-trap-GC/mass spec- toxicity, and that were not already included in the ICR, were trometry (MS) method was used to analyze for VOCs and selected for a new U.S. occurrence study (23). Highest in this certain volatile chemicals that have been reported as possible ranking were the bromonitromethanes, which recently have DBPs (mono- and dihalogenated
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